Skip to main content
SpringerLink
Log in

Multicomponent synthesis of spiroannulated hybrid molecules with preferred substructures using indium triflate as a sustainable catalyst

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

An efficient and environmentally benign In(OTf)3 catalysed multicomponent approach for the synthesis of spiroannulated pyridopyrimidines, chromenopyridines, indenopyridines and quinolines has been presented for the first time. The current approach uses an indium triflate as a catalyst in a one-pot four-component reaction of isatin, malononitrile, 1,3-Diketone, and 4-ethylaniline in ethyl alcohol. The current protocol presents multiple advantages that including operational simplicity with easy workup, moderate reaction conditions, shorter reaction times (25–40 min), excellent yields (85–96%) with superior atom economy, green and environmentally benign reaction conditions due to the use of recyclable and reusable non-toxic metal catalyst.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Scheme 1.
Scheme 2.
Scheme 3.
Fig. 3

Similar content being viewed by others

References

  1. Y. Wang, A.A. Cobo, A.K. Franz, Org. Chem. Front. 8, 4315 (2021)

    Article  CAS  Google Scholar 

  2. M.B.J. Atkinson, S.O. Reynoso, R.E. Luna, D.K. Bwambok, M.M. Thuo, RSC Adv. 5, 597 (2015)

    Article  CAS  Google Scholar 

  3. A. Domling, W. Wang, K. Wang, A.C.S. Pub, Chem. Rev. 112, 3083 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. A. Chaudhary, Mol. Div. 25, 1211 (2021)

    Article  CAS  Google Scholar 

  5. H. Mousavi, Int. J. Bio. Mac. 186, 1003 (2021)

    Article  CAS  Google Scholar 

  6. J. Akhtar, A.A. Khan, Z. Ali, R. Haider, M.S. Yar, Eur. J. Med. Chem. 125, 143 (2017)

    Article  CAS  PubMed  Google Scholar 

  7. S. Nandi, R. Jamatia, R. Sarkar, F. K. Sarkar, S. Alam, A. K. Pal, Chem. Sel. 7, (2022)

  8. V. V. Chernyshov, I. I. Popadyuk, O.I. Yarovaya, N. F. Salakhutdinov, Top. Curr. Chem. 380 (2022)

  9. E. Zarenezhad, M. Farjam, A. Iraji, J. Mol. Struct. 1230, 129833 (2021)

    Article  CAS  Google Scholar 

  10. T.H. Chen, C.C. Nieh, Y.C. Shih, C.Y. Ke, W.L. Tseng, RSC Adv. 5, 45158 (2015)

    Article  CAS  Google Scholar 

  11. R. Ghosh, J.B. Vitor, E. Mendes, A. Paulo, P.C. Acharya, ACS Ome. 5, 27332 (2020)

    Article  CAS  Google Scholar 

  12. M. Salimi, R. Sandaroos, F.E. Nasrabadi, J. Iran. Chem. Soc. 18, 1 (2021)

    Article  CAS  Google Scholar 

  13. T.L. Pavlovska, R. Gr. Redkin, V.V. Lipson, D.V. Atamauk, Mol. Div. 20, 299 (2016)

  14. S.B. Singh, K. Tiwari, P.K. Verma, M. Srivastava, K.P. Tiwari, J. Singh, Supramol. Chem. 25, 255 (2013)

    Article  CAS  Google Scholar 

  15. E.K. Reddy, C. Remya, A.M. Sajith, K.V. Dileep, C. Sadasivan, S. Anwar, RSC Adv. 6, 77431 (2016)

    Article  Google Scholar 

  16. B. Dam, R. Jamatia, A. Gupta, A.K. Pal, A.C.S. Sus, Chem. Eng. 5, 11459 (2017)

    CAS  Google Scholar 

  17. I. Ejaz, M.A. Javed, M.S. Jan, M. Ikram, A. Sadiq, S. Ahmad, U. Rashid, Bioorg. Med. Chem. Lett. 64, 128668 (2022)

    Article  CAS  PubMed  Google Scholar 

  18. N. Kaur, P. Singh, P. Kaur, A.N. Yadav, K. Singh, J. Het. Chem. 57, 3622 (2020)

    Article  CAS  Google Scholar 

  19. A.A. Patravale, A.H. Gore, D.R. Patil, G.B. Kolekar, M.B. Deshmukh, P.V. Anbhule, Ind. Eng. Chem. Res. 53, 16568 (2014)

    Article  CAS  Google Scholar 

  20. P. Yadav, K. Shah, Chem. Bio. Drug Des. 97, 633 (2020)

    Article  Google Scholar 

  21. N.E.A.A. El-sattar, E.H.K. Badawy, E.Z. Elrazaz, N.S.M. Ismail, RSC Adv. 11, 4454 (2021)

    Article  Google Scholar 

  22. K. Leškovskis, A. Mishnev, I. Novosjolova, M. Turks, J. Mol. Str. 1269, 133784 (2022)

    Article  Google Scholar 

  23. B. Sabour, M.H. Peyrovi, M. Hajimohammadi, Res. Chem. Intermed. 41, 1343 (2015)

    Article  CAS  Google Scholar 

  24. H.K. Singh, A. Kamal, S.K. Maury, A.K. Kushwaha, V. Srivastava, S. Singh, Org. Biomol. Chem. 21, 4854 (2023)

    Article  CAS  PubMed  Google Scholar 

  25. M.M. Gineinah, M.N.A. Nasr, S.M.I. Badr, W.M. El-Husseiny, Med. Chem. Res. 22, 3943 (2013)

    Article  CAS  Google Scholar 

  26. R.N. Kumar, G.J. Dev, N. Ravikumar, D.K. Swaroop, B. Debanjan, G. Bharath, B. Narsaiah, S.N. Jain, A.G. Rao, Bioorg. Med. Chem. Lett. 26, 2927 (2016)

    Article  Google Scholar 

  27. R. Aryan, H. Beyzaei, M. Nojavan, F. Pirani, H.S. Delarami, M. Sanchooli, Mol. Div. 23, 93 (2019)

    Article  CAS  Google Scholar 

  28. R. Sarma, K.J. Borah, Y. Dommaraju, D. Prajapati, Mol. Div. 15, 697 (2011)

    Article  CAS  Google Scholar 

  29. A. Shaabani, H. Sepahvand, M.B. Boroujeni, M.T. Faroghi, Mol. Div. 21, 147 (2017)

    Article  CAS  Google Scholar 

  30. D.A. Ibrahim, N.S. Ismail, Eu. J. Med. Chem. 46, 5825 (2011)

    Article  CAS  Google Scholar 

  31. D. Bhurta, S.B. Bharate, Med. Res. Rev. 42, 654 (2022)

    Article  CAS  PubMed  Google Scholar 

  32. P. Anaikutti, M. Selvaraj, J. Prabhakaran, T. Pooventhiran, T.C. Jeyakumar, R. Thomas, P. Makam, J. Mol. Str. 1266, 133464 (2022)

    Article  CAS  Google Scholar 

  33. M. Goswami, A. Dutta, P. Paul, R. Nongkhlaw, Chem. Sel. 6, 9684 (2021)

    CAS  Google Scholar 

  34. M.M. Kandeel, A.M. Kamal, E.K.A. Abdelall, H.A.H. Elshemy, Eur. J. Med. Chem. 59, 183 (2013)

    Article  CAS  PubMed  Google Scholar 

  35. A.M. Abdelmoniem, S.A.S. Ghozlan, D.M. Abdelmoniem, A.H.M. Elwahy, I.A. Abdelhamid, J. Het. Chem. 54, 2844 (2017)

    Article  CAS  Google Scholar 

  36. S.T. Chung, W.H. Huang, C.K. Huang, F.C. Liu, R.Y. Huang, C.C. Wu, A.R. Lee, Res. Chem. Intermed. 42, 1195 (2016)

    Article  CAS  Google Scholar 

  37. A.M. Shestopalov, Y.M. Litvinov, L.A. Rodinovskaya, O.R. Malyshev, M.N. Semenova, V.V. Semenov, A.C.S. Comb, Sci. 14, 484 (2012)

    CAS  Google Scholar 

  38. D.D. Haveliwala, N.R. Kamdar, P.T. Mistry, S.K. Patel, Helv. Chim. Acta 96, 897 (2013)

    Article  CAS  Google Scholar 

  39. N.R. Kamdar, D.D. Haveliwala, P.T. Mistry, S.K. Patel, Eur. J. Med. Chem. 45, 5056 (2010)

    Article  CAS  PubMed  Google Scholar 

  40. C. Wang, Z. Lai, H. Xie, S. Cui, Ang. Chem. Inter. Ed. 60, 5147 (2020)

    Article  Google Scholar 

  41. A. Sahu, S. Mishra, P. Sahu, A. Gajbhiye, R.K. Agrawal, Curr. Organocat. 5, 137 (2018)

    Article  CAS  Google Scholar 

  42. J.P. Sestelo, L.A. Sarandeses, M.M. Martínez, L.A. Marañón, Org. Biomol. Chem. 16, 5733 (2018)

    Article  Google Scholar 

  43. B. Karami, S. Khodabakhshi, S. Karami, Croat. Chem. Acta 87, 23 (2014)

    Article  CAS  Google Scholar 

  44. D. Kundu, A. Majee, A. Hajra, Tet. Lett. 50, 2668 (2009)

    Article  CAS  Google Scholar 

  45. H. Yanai, T. Sakiyama, T. Oguchi, T. Taguchi, Tet. Lett. 53, 3161 (2012)

    Article  CAS  Google Scholar 

  46. V. Narsaiah, J.K. Kumar, P. Narsimha, Synthesis 10, 1609 (2010)

    Article  Google Scholar 

  47. S. Swami, A. Agarwala, R. Shrivastava, Mol. Div. 21, 81 (2017)

    Article  CAS  Google Scholar 

  48. D. Habibi, P. Rahmani, F. Ahmadi, H. Bokharaei, Z. Kaboudvand, Lett. Org. Chem. 11, 145 (2014)

    Article  CAS  Google Scholar 

  49. Q.H. To, Y.R. Lee, S.H. Kim, Bull. Korean Chem. Soc. 33 (2012)

  50. N. Poomathi, P.T. Perumal, S. Ramakrishna, Green Chem. 19, 2524 (2017)

    Article  CAS  Google Scholar 

  51. D. Prajapati, M. Gohain, Beilstein J. Org. Chem. 2 (2006)

  52. A. Prajapati, M. Kumar, R. Thakuria, A.K. Basak, Tetr. Lett. 60, 150955 (2019)

    Article  CAS  Google Scholar 

  53. A. Prajapati, M. Kumar, R. Thakuria, A.K. Basak, Tet. Lett. 61, 152347 (2020)

    Article  CAS  Google Scholar 

  54. S. Khandelwal, Y.K. Tailor, M. Kumar, J. Mol. Liq. 215, 345 (2016)

    Article  CAS  Google Scholar 

  55. M. Kumar, K. Sharma, A.K. Arya, Tet. Lett. 53, 4604 (2012)

    Article  CAS  Google Scholar 

  56. Y.K. Tailor, S. Khandelwal, R. Gopal, E. Rushell, A. Prajapati, M. Kumar, Chem. Sel. 2, 11055 (2017)

    CAS  Google Scholar 

  57. A. Rajawat, S. Khandelwal, M. Kumar, RSC Adv. 4, 5105 (2014)

    Article  CAS  Google Scholar 

  58. A. Verma, D.K. Arya, S. Kumar, G. Pathak, V. Khatri, Res. Chem. Intermed. 49, 4865 (2023)

    Article  CAS  Google Scholar 

  59. H. Atharifar, A. Keivanloo, B. Maleki, M. Baghayeri, H. Alinezhad, Res. Chem. Intermed. (2023)

  60. B. Maleki, O. Reiser, E. Esmaeilnezhad, H.J. Choi, Polyhedron 162, 129 (2019)

    Article  CAS  Google Scholar 

  61. B. Maleki, M. Chahkandi, R.Tayebee, S. Kahrobaei, H. Alinezhad, S. Hemmati, Appl. Organometal. Chem. 33, Issue 10, e5118 (2019)

  62. B. Maleki, S.S. Ashrafi, R. Tayebee, RSC Adv. 4, 41521 (2014)

    Article  CAS  Google Scholar 

  63. B. Maleki, Org. Prep. Pro. Inter. 47, 173 (2015)

    Article  CAS  Google Scholar 

  64. N.C. Dige, D.M. Pore Ful, Synth. Commun. 45, 2498 (2015)

  65. F. Najafizadeh, K.R. Moghadam, S.Y. Kalurazi, J. Chem. Res. 1 (2020)

  66. P. Tong, Z. Sun, S. Wang, Y. Zhang, Y. Li, J. Org. Chem. 84, 13967 (2019)

  67. R. Ghahremanzadeh, M.M. Moghaddam, A. Bazgir, M.M. Akhondi, C. J. Chem. 30, 321 (2012)

    CAS  Google Scholar 

  68. A. Mondal, B. Naskar, S. Goswami, C. Prodhan, K. Chaudhuri, C. Mukhopadhyay, Mol. Div. 24, 93 (2020)

    Article  CAS  Google Scholar 

  69. H.Z. Fazlelahi, P.N. Moghadam, M.M. Baradarani, J.A. Jouleb, J. Het. Chem. 57, 3673 (2020)

    Article  CAS  Google Scholar 

  70. D. Azarifar, M. Ghaemi, M. Jaymand, R. Karamian, M. Asadbegy, F. Ghasemlou, Mol. Div. 26, 891 (2022)

    Article  CAS  Google Scholar 

  71. H. Naeimi, Z. Rashid, A.H. Zarnani, R. Ghahremanzadeh, N. J. Chem. 38, 348 (2014)

    Article  CAS  Google Scholar 

  72. S. Kavyani, R. Baharfar, Appl. Org. Chem. 34, e5560 (2020)

    Article  CAS  Google Scholar 

  73. A.A. Mohammadi, S. Taheri, A. Amouzegar, J. Het. Chem. 54, 2085 (2016)

    Article  Google Scholar 

  74. A. Mondal, C. Mukhopadhyay, A.C.S. Comb, Science 17, 404 (2015)

    CAS  Google Scholar 

  75. A.R. Khorrami, P. Kiani, A. Bazgir, M. für Chem. Chem. Mon. 142, 287 (2011)

    Article  CAS  Google Scholar 

  76. G.I. Shakibaei, A. Feiz, H. Reza Khavasi, A.A. Soorki, A. Bazgir, ACS Comb. Sci. 13, 96 (2011)

    Article  CAS  PubMed  Google Scholar 

  77. W.H. Zhang, M.N. Chen, Y. Hao, X. Jiang, X.L. Zhou, Z.H. Zhang, J. Mol. Liq. 278, 124 (2019)

    Article  CAS  Google Scholar 

  78. D.R. Chandam, A.G. Mulik, D.R. Pati, A.P. Patravale, D.R. Kumbhar, M.B. Deshmukh, J. Mol. Liq. 219, 573 (2016)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Rajasthan, Jaipur, 302004, India

    Asha Verma, Vineeta Khatri & Gargi Pathak

  2. Department of Chemistry, Ramjas College, University of Delhi, New Delhi, 110007, India

    Sandeep Kumar

  3. Department of Chemistry, Acharya Narendra Dev College, University of Delhi, New Delhi, 110019, India

    Dinesh Kumar Arya

Authors
  1. Asha Verma
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sandeep Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Vineeta Khatri
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Gargi Pathak
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Dinesh Kumar Arya
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

Asha Verma carried out the synthesis of all the compounds. Sandeep Kumar, Vineeta Khatri, Gargi Pathak helped to design the project and to compile the manuscript. The research was carried out in the supervision of Dinesh Kumar Arya.

Corresponding author

Correspondence to Dinesh Kumar Arya.

Ethics declarations

Competing interests

The authors declare no competing interests.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Verma, A., Kumar, S., Khatri, V. et al. Multicomponent synthesis of spiroannulated hybrid molecules with preferred substructures using indium triflate as a sustainable catalyst. Res Chem Intermed 50, 251–264 (2024). https://doi.org/10.1007/s11164-023-05177-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-023-05177-2

Keywords

Search

Navigation